Hexane → Ethyl 2-Cyano-3-(5,6,7,8-tetrahydro-1-isoquinolylamino)-acrylate

HRID 1707033Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][N:3]=1.C(O[CH:15]=[C:16]([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C.CCCCCC>C1(C)C=CC=CC=1>[C:22]([C:16](=[CH:15][NH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][N:3]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:23]

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of 1-amino-5,6,7,8-tetrahydroisoquinoline [2.96 g., 0.02 mole; E. Ochiai and Y. Kawazoe, Pharm. Bull. (Tokyo), 5, 606 (1957)] and ethyl ethoxymethylenecyanoacetate (3.38 g., 0.02 mole) in toluene (8 ml.) was heated by means of an oil bath maintained at 105° C. for 15 minutes. The cooled solution was poured into Skellysolve B (175 ml.) with good stirring. The mixture was triturated and cooled with an ice bath. The mixture was filtered and the collected gummy solid recrystallized from cyclohexane to give the title compound (4.1 g., 75%), m.p. 116°-120° C. The product was recrystallized from cyclohexane to give analytical material, m.p. 121°-123° C.

Workup

customThe mixture was triturated
temperaturecooled with an ice bath
filtrationThe mixture was filtered
customthe collected gummy solid recrystallized from cyclohexane

Sources & evidence

ORD record: ord-58bb4b081a3844659ee8a4e61e593a7b
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04209620

Reaction notes

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